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Design, facile synthesis and anthelmintic activity of new O-substituted 6-methoxybenzothiazole-2-carbamates. Part II†

Abstract

In framework of pursuing design and synthesis of new series of substituted 6-methoxybenzothiazole-2-carbamate as potential anthelmintics and as continuation of expended efforts in part I, a focus has been set to develop novel compounds with enhanced anthelmintic activity having blocked 6-position benzothiazole with side chains of different polarities. Guided by findings in preceding part, reporting paramphistomicidal activity of oxadiazoline derivatives V and VI, an emphasis was created to synthesize target benzothiazoles designed to comprise some planar heterocyclic ring systems; as 1,3,4-oxadiazoles and 1,2,4-triazoles baring variety of hydrophobic and hydrophilic components. Synthesis of desired compounds was primarily achieved by cyclization of 6-acetohydrazide 1. In vitro paramphistomicidal activity of all synthesized carbamates was evaluated. Four synthesized carbamates exhibited notable activity. Compound 24, methyl 6-[(5-(4-bromophenacylsulfanyl)-[1,3,4]-oxadiazol-2-yl)methoxy]benzothiazole-2-carbamate, displayed equipotent effect to reference drug Oxyclozanide at a concentration of 80 µg/ml. Compounds 9, 10 and 23 showed high orders of anthelmintic effect. Structural computational study attempting polar nature and hydrophilic-lipophilic properties of synthesized carbamates was undertaken discussing their structure-activity relationship (SAR). Besides, pharmacophore mapping was performed using eight active compounds as training set. The generated pharmacophore model revealed five common features and was validated using fenbendazole, triclabendazole and triclabendazole sulfoxide.

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Publication details

The article was received on 17 Mar 2017, accepted on 08 May 2017 and first published on 12 May 2017


Article type: Research Article
DOI: 10.1039/C7MD00140A
Citation: Med. Chem. Commun., 2017, Accepted Manuscript
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    Design, facile synthesis and anthelmintic activity of new O-substituted 6-methoxybenzothiazole-2-carbamates. Part II†

    A. M. M.E. Omar, O. M. Aboulwafa, D. A. E. Issa, M. S.M. El-Shoukrofy, M. E. Amr and I. M. El-Ashmawy, Med. Chem. Commun., 2017, Accepted Manuscript , DOI: 10.1039/C7MD00140A

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